HCID 66670645, compound → (3R,4S)-tert-Butyl 3-(bis(4-Methoxyphenyl)(phenyl)Methoxy)-4-((Methylsulfonyl)oxy)pyrrolidine-1-carboxylate

HRID 1896210Notes

Reaction equation

HRID 1896210 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[CH:10]([CH2:11]2)[O:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:14]1([Mg]Br)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CC1CCCO1.[Cu](I)I>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:10]([OH:9])[CH2:11]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 66670645HCID 66670645, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 73553444(3R,4S)-tert-Butyl 3-(bis(4-Methoxyphenyl)(phenyl)Methoxy)-4-((Methylsulfonyl)oxy)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 73012-MethyltetrahydrofuranSolvent

Procedure

Oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (3 g, 16 mmol), was dissolved in 2-methyl-tetrahydrofuran (5 mL) and added dropwise to a solution of phenylmagnesium bromide (1.5 eq, 24.3 mL of a 1.0 M solution) and copper iodide (0.05 eq) at 0° C. The reaction was allowed to warm to room temperature and stir for 18 h. Reaction was cooled to 0° C. and quenched with sat. NH4Cl solution and extracted with EtOAc. Organic was washed with NaHCO3 and brine and dried over Na2SO4 and the solvent removed. Residue was purified by column chromatography on SiO2 (15-40% EtOAc/HEptane) which gave the title compound Ia as a yellow oil (3.59 g).

Workup

  1. customReaction
  2. temperaturewas cooled to 0° C.
  3. customquenched with sat. NH4Cl solution
  4. extractionextracted with EtOAc
  5. washOrganic was washed with NaHCO3 and brine
  6. dry with materialdried over Na2SO4
  7. customthe solvent removed
  8. customResidue was purified by column chromatography on SiO2 (15-40% EtOAc/HEptane) which

Sources & evidence

ORD record
ord-9e54190928a24422ad5990a5ef525f6a
Source dataset
uspto-grants-2013_08
Patent number
US08518952B2

Reaction notes

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